29/f anal beginner or pussy stretching
 

I have about 2 hours available for dares or punishments. I currently have clamps on my nipples from a punishment I received yesterday. I deserve to be punished because I’ve been looking at porn instead of cleaning my house.

I want to begin exploring anal and pussy stretching. I am a true anal beginner. The only thing I’ve had in my asshole is ice cubes. I have realized my asshole and pussy are not living up to their full potential so I need tasks to begin getting them there. I am open to tasks that build over multiple days.

I have: nipple clamps, toothpaste, a dildo, belt, wooden spoon, icy hot, ice cubes, a vibrator, and other household items.

Let's start with a classic: one pen up your ass, two pens up your ass, three pens up your ass and so on. How many pens can you tak up your ass?

I’ll try this now and report back! Thank you.

I was only able to fit 2. The second one was uncomfortable.

Would love anal or pussy stretching tasks to work on over the weekend. You can pm me or post them here.

It means that you need more training, then it will be a long training weekend.

You'll spend your weekend having your ass filled. Start saturday as you wake up inserting two pens, keeping them inserted while doing your daily life occupations and/or whatever the GD guys will choose for you.

When you start feeling comfortable with two, or after no more than four hours of insertion, you will add the third one, then the fourth after no more than six hours after the third. Try to keep the four pens as long as you can, but go down to three at least one hour before going to sleep, to leave time to your hole to appreciate the comfort to have only three pens in. You'll remove all the pens to sleep, because it's not safe to have pens inserted since you don't control your movements while sleeping, and the pens could hurt you (things would be different using plugs).

On sunday you'll repeat the same routine, but starting with three, then adding the fourth after no more than 4 hours. At this point, the goal would be to insert the fifth, but if you feel too much uncomfortable with four, you could train your hole alternating stretching and relax, swapping every 30 minutes between 3 and 4, and maybe increasing the time with 4 pens and reducing the time with 3 as long as you get accustomed. Finally inserting the fifth would be a success, but even getting used to have 4 inserted without too much discomfort would be a good result.

Keeping you horny could be of help, so you are encouraged to edge as much as you can, to keep you constantly escited, but orgasms will be allowed on saturday only while/after you have inserted 4 pens, and on sunday only while/after you have inserted five pens, or, if you don't reach 5, when you're going to sleep, while (and after) having 4 pens inserted. No orgasm is allowed if you don't reach the 4 pens inserted.

Thank you Sir. I’ll definitely be doing this.

Since you are also interested in pussy stretching, why don't you let us know hoa many pens you can fit in your pussy as well?

Thank you. I was able to fit 6 sharpies in my pussy.

Good girl, I expect a detailed report.

Of course, Sir! I’m off work today so may I start today?

Of course, I appreciate your dedication.

Let's see how many pens you'll be able to insert until it's time to go on bed (btw, what's your timezone?). You'll let me know how many you will be able to bear with ease and how many with discomfort (and, why not, how many with pain, but be careful), it will help to understand if the given goals for the weekend might be corrected.

Thank you Sir. I’ll insert the first 2 now. I’m in Est. It’s 10 am here.

Well done so far...

If it helps with your horniness (as per redcamel's wise suggestion), I'd put nipple clamps on too (for 5 minutes before each new pen insertion, and keeping them 5 more minutes after).

Oh, and don't forget to use some lube: part of the discomfort may depends on a lack of lubrication

Thank you! I will use the nipple clamps.